title: Synthesis and properties of 2'-O,4'-C-ethyleneoxy bridged 5-methyluridine.
abstract: 2'-O,4'-C-Ethyleneoxy bridged 5-methyluridine (EoNA-T), possessing a seven-membered linkage and an anomeric 4'-carbon, was synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. The EoNA-modified oligonucleotides significantly stabilized the duplexes with single-stranded RNA and triplexes with double-stranded DNA relative to the natural oligonucleotide and oligonucleotides modified by another seven-membered bridged 5-methyluridine, 2',4'-BNA(COC)-T. In addition, EoNA-T showed excellent nuclease resistance.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita 565-0871, Japan. hari@phs.osaka-u.ac.jp
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Hari
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Morikawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Osawa
authors.forename: Satoshi
authors.initials: S
authors.lastname: Obika
mesh_terms: D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D016376:Oligonucleotides, Antisense / Q000737:chemistry*; D012313:RNA / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009841:Oligonucleotides; D016376:Oligonucleotides, Antisense; C009182:ribothymidine; D012313:RNA; D004247:DNA; D014529:Uridine